Parallel solid phase synthesis of tetrasubstituted diethylenetriamines via selective amide alkylation and exhaustive reduction of N-acylated dipeptides

Tetrahedron

Volumn 55, Issue 2, 1999, Pages 335-344

  Nefzi, Adel ^a   Ostresh, John M ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; DIETHYLENETRIAMINE; DIPEPTIDE; POLYAMINE;

ACYLATION; ALKYLATION; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; RACEMIC MIXTURE; REDUCTION; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 0033534581     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01043-6     Document Type: Article

References (22)

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10. 3 were derived from the following carboxylic acids: 1-phenyl-1-cyclopropane carboxylic acid, m-tolylacetic acid, 3-fluorophenylacetic acid, (α,α,α)-trifluoro-m-tolylacetic acid, p-tolylacetic acid, 3-methoxyphenylacetic acid, 4-methoxyphenylacetic acid, 4-ethoxyphenylacetic acid, 4-isobutyl-α-methylphenylacetic acid, 3,4-dichlorophenylacetic acid, 3,5-bis(trifluoromethyl)-phenylacetic acid, phenylacetic acid, hydrocinnamic acid, 4-phenylbutyric acid, butyric acid, heptanoic acid, isobutyric acid, isovaleric acid, 4-methylvaleric acid, trimethylacetic acid, tertbutylacetic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, cycloheptanecarboxylic acid, acetic acid, cyclobutanecarboxylic acid, cyclopentanecarboxylic acid, cyclohexanepropionic acid, 4-methyl-1-cyclohexanecarboxylic acid, 4-tert-butyl-cyclohexanecarboxylic acid, 1-adamantaneacetic acid, 3,3-diphenylpropionic acid, dicyclohexylacetic acid, indole-3-acetic acid, 1-naphthylacetic acid, 3-(3,4,5)-trimethoxyphenylpropionic acid, 2-norbornaneacetic acid, cyclopentylacetic acid, 2-ethylbutyric acid.
11. The yields obtained in all cases are higher then 80% relative to the initial loading of the resin.
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